(2S,3S)-1,4-di-O-benzyl-2,3-O-(3-pentylidene)threitol | 1472686-46-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S)-1,4-di-O-benzyl-2,3-O-(3-pentylidene)threitol
• CAS: 1472686-46-6
• 化学式: C₂₃H₃₀O₄
• 分子量: 370.489
• InChiKey: AQZOISUYQDSUBJ-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  27.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-1,4-di-O-benzyl-2,3-O-(3-pentylidene)threitol 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以75%的产率得到(-)-1,4-O-二苯基-L-苏醇
  参考文献：
  名称：

  An optimized synthetic route for the preparation of the versatile chiral building block 1,4-di-O-benzylthreitol

  摘要：

  An improved five-step procedure has been applied to synthesize enantiopure l- and d-1,4-di-O-benzylthreitol out of readily available l- and d-tartaric acid. Through the use of modern reagents and enhanced work-up conditions these useful auxiliaries were obtained in quite perfect yields. In addition, accurate H-1 and C-13 NMR resonance assignments of all synthesized compounds were performed by 2D NMR spectroscopy.

  DOI：

  10.1007/s00706-013-1100-x
• 作为产物：
  描述：

  (4R,5R)-dimethyl 2,2-diethyl-1,3-dioxolane-4,5-dicarboxylate 在 甲醇 、 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 27.34h， 生成 (2S,3S)-1,4-di-O-benzyl-2,3-O-(3-pentylidene)threitol
  参考文献：
  名称：

  An optimized synthetic route for the preparation of the versatile chiral building block 1,4-di-O-benzylthreitol

  摘要：

  An improved five-step procedure has been applied to synthesize enantiopure l- and d-1,4-di-O-benzylthreitol out of readily available l- and d-tartaric acid. Through the use of modern reagents and enhanced work-up conditions these useful auxiliaries were obtained in quite perfect yields. In addition, accurate H-1 and C-13 NMR resonance assignments of all synthesized compounds were performed by 2D NMR spectroscopy.

  DOI：

  10.1007/s00706-013-1100-x